N-methyl-L-phenylalanine methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-L-phenylalanine methyl ester
• 英文别名: N-methylphenylalanine methyl ester；methyl (2S)-2-(methylamino)-3-phenylpropanoate
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: VJXKYPIBDBDIJL-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-L-phenylalanine methyl ester 在 甲醇 、 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以71%的产率得到3-苯丙酸甲酯
  参考文献：
  名称：

  Reductive deamination of α-amino carbonyl compounds by means of samarium iodide

  摘要：

  α-氨基羰基化合物在SmI2存在下于THF-HMPA体系中及质子源作用下反应，生成了脱氨产物，其中断裂发生在氮原子与羰基α位碳之间。

  DOI：

  10.1039/a903073e
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-methyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  A new inhibitor design strategy for carboxypeptidase A as exemplified by N -(2-chloroethyl)- N -methylphenylalanine

  摘要：

  N-(2-Chloroethyl)-N-methylphenylalanine was designed and synthesized in an optically active form as a novel class of mechanism-based inactivator for carboxypeptidase A (CPA). It was anticipated that the chloroethylamino moiety of the CPA bound inhibitor undergoes an intramolecular S(N)2 reaction to generate a chemically reactive species (an aziridinium ion) which is expectedly subjected to a nucleophilic attack by the carboxylate of Glu-270, leading to covalent modification of the carboxylate. The irreversible nature of the inhibition of CPA by the inhibitor was supported by the kinetic data: the enzyme lost its enzymic activity in a time-dependent manner in the presence of the inhibitor and the inactivated CPA failed to regain the activity upon dialysis. Interestingly, the (R)-isomer that belongs to the D-series was more potent than its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00239-x

文献信息

• N‐Methylated Peptide Synthesis via Generation of an Acyl N‐Methylimidazolium Cation Accelerated by a Brønsted Acid
  作者：Yuma Otake、Yusuke Shibata、Yoshihiro Hayashi、Susumu Kawauchi、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.202002106

  日期：2020.7.27

  formation remains a critical aspect of N‐methylated peptide synthesis. In this study, we synthesized a variety of dipeptides in high yields, without severe racemization, from equivalent amounts of amino acids. Highly reactive N‐methylimidazolium cation species were generated in situ to accelerate the amidation. The key to success was the addition of a strong Brønsted acid. The developed amidation enabled

  牢固的酰胺键形成的发展仍然是N-甲基化肽合成的关键方面。在这项研究中，我们从等量的氨基酸中高收率合成了各种二肽，而没有严重的消旋作用。高反应性的N-甲基咪唑鎓阳离子原位生成以加速酰胺化反应。成功的关键是加入强力的布朗斯台德酸。与常规酰胺化的结果相比，开发的酰胺化使得能够在较短的时间内以较高的产率合成大体积的肽。另外，可以通过使用微流反应器或常规烧瓶来进行酰胺化。天然存在的大体积N-甲基化肽，蝶酰胺I-IV的首次全合成。根据实验结果和理论计算，
• The First Total Synthesis of (−)-Benzomalvin A<i>via</i>Intramolecular Aza-Wittig Reactions
  作者：Toshiyuki Sugimori、Tomohiro Okawa、Shoji Eguchi、Eiji Yashima、Yoshio Okamoto

  DOI：10.1246/cl.1997.869

  日期：1997.9

  The first total synthesis of (−)-benzomalvin A 1, which possesses quinazolin-4(3H)-one moiety and 1,4-benzodiazepin-5-one moiety, was described. Both of 6- and 7-membered ring skeletons were efficiently constructed by intramolecular aza-Wittig reactions as the key reactions.

  (−)-benzomalvin A 1 的首次全合成被报道，该化合物具有喹唉-4(3H)-酮部分和1,4-苯二氮杂革-5-酮部分。通过分子内的氮杂Wittig反应高效构建了6元环和7元环骨架，这些反应被作为关键反应。
• Reductive N-methylation of amines with calcium hydride and Pd/C catalyst
  作者：Carole Guyon、Marie-Christine Duclos、Estelle Métay、Marc Lemaire

  DOI：10.1016/j.tetlet.2016.05.094

  日期：2016.7

  The methylation of amines by paraformaldehyde in the presence of calcium hydride as a source of hydrogen and palladium on charcoal as catalyst was studied. Depending on the quantity of paraformaldehyde, monomethylated and dimethylated amines were selectively and efficiently prepared in one pot with good yields.

  研究了在氢化钙作为氢源和钯在木炭上的催化作用下，低聚甲醛对胺的甲基化作用。根据多聚甲醛的量，在一锅中以高收率选择性地和有效地制备了单甲基化和二甲基化的胺。
• Compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Athena Neurosciences, Inc.

  公开号：US06559127B1

  公开（公告）日：2003-05-06

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  揭示了结合VLA-4的化合物。其中某些化合物还抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病方面非常有用，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• Transition Metal‐Free <i>N‐</i> Arylation of Amino Acid Esters with Diaryliodonium Salts
  作者：Gabriella Kervefors、Leonard Kersting、Berit Olofsson

  DOI：10.1002/chem.202005351

  日期：2021.3.26

  A transition metal‐free approach for the N‐arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional

  已经开发出一种用于氨基酸衍生物N芳基化的无过渡金属方法。该方法的关键是使用带有茴香基配体的不对称二芳基碘盐，这被证明对于获得高化学选择性和产率非常重要。范围包括缺电子、富电子和空间位阻芳基与各种不同官能团的转移。此外，环状二芳基碘鎓盐成功地用于芳基化。获得保留对映体过量的N-芳基化产物。